Synthesis of 3′-N-Substituted 3′-Amino-3′-Deoxythymidine Derivatives
A series of 3′-N-substituted 3′-amino-3′-deoxythymidine derivatives with alkyl, alkenyl and alkylaryl substituents was synthesized by two methods. The first method involved the reaction of 1-(2,3-dideoxy-3-0-mesyl-5-0-trityl-β-D-threo-pentofuranosyl)thymine with an appropriate amine. In the second m...
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| Veröffentlicht in: | Nucleosides & nucleotides 1993-11, Vol.12 (9), p.951-966 |
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| container_title | Nucleosides & nucleotides |
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| creator | Celewicz, Lech Urjasz, Wojciech Golankiewicz, Krzysztof |
| description | A series of 3′-N-substituted 3′-amino-3′-deoxythymidine derivatives with alkyl, alkenyl and alkylaryl substituents was synthesized by two methods. The first method involved the reaction of 1-(2,3-dideoxy-3-0-mesyl-5-0-trityl-β-D-threo-pentofuranosyl)thymine with an appropriate amine. In the second method, 3′-amino-5′-0-trityl-3′-deoxy-thymidine served as a synthetic precursor which was reacted with an appropiate aldehyde or ketone followed by sodium borohydride reduction. An improved synthesis of 3′-amino-3′-deoxythymidine from 3′ -azido-5′-0-trityl-3′-deoxythymidine using sodium borohydride was also described. |
| doi_str_mv | 10.1080/07328319308018565 |
| format | Article |
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The first method involved the reaction of 1-(2,3-dideoxy-3-0-mesyl-5-0-trityl-β-D-threo-pentofuranosyl)thymine with an appropriate amine. In the second method, 3′-amino-5′-0-trityl-3′-deoxy-thymidine served as a synthetic precursor which was reacted with an appropiate aldehyde or ketone followed by sodium borohydride reduction. An improved synthesis of 3′-amino-3′-deoxythymidine from 3′ -azido-5′-0-trityl-3′-deoxythymidine using sodium borohydride was also described.</description><identifier>ISSN: 0732-8311</identifier><identifier>EISSN: 2332-3892</identifier><identifier>DOI: 10.1080/07328319308018565</identifier><identifier>CODEN: NUNUD5</identifier><language>eng</language><publisher>Monticello, NY: Taylor & Francis Group</publisher><subject>Carbohydrates. 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Nucleosides and nucleotides</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Nucleosides, nucleotides and oligonucleotides</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><toplevel>online_resources</toplevel><creatorcontrib>Celewicz, Lech</creatorcontrib><creatorcontrib>Urjasz, Wojciech</creatorcontrib><creatorcontrib>Golankiewicz, Krzysztof</creatorcontrib><collection>Pascal-Francis</collection><collection>CrossRef</collection><jtitle>Nucleosides & nucleotides</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Celewicz, Lech</au><au>Urjasz, Wojciech</au><au>Golankiewicz, Krzysztof</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of 3′-N-Substituted 3′-Amino-3′-Deoxythymidine Derivatives</atitle><jtitle>Nucleosides & nucleotides</jtitle><date>1993-11-01</date><risdate>1993</risdate><volume>12</volume><issue>9</issue><spage>951</spage><epage>966</epage><pages>951-966</pages><issn>0732-8311</issn><eissn>2332-3892</eissn><coden>NUNUD5</coden><abstract>A series of 3′-N-substituted 3′-amino-3′-deoxythymidine derivatives with alkyl, alkenyl and alkylaryl substituents was synthesized by two methods. 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| subjects | Carbohydrates. Nucleosides and nucleotides Chemistry Exact sciences and technology Nucleosides, nucleotides and oligonucleotides Organic chemistry Preparations and properties |
| title | Synthesis of 3′-N-Substituted 3′-Amino-3′-Deoxythymidine Derivatives |
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